About Simon Stapleton


Virginia Estate Planning Attorney

Simon Stapleton
Principal Attorney

With nearly 25 years of experience, Simon understands the intricacies and significance of Estate Planning and Asset Protection. In addition, he specializes in Medicaid and crisis planning, as well as assisting our Veterans obtain their well-deserved benefits.

Licensed to practice in Virginia and the United Kingdom, Simon has law degrees from Essex University, in the United Kingdom and from the University of Richmond, T.C. Williams School of Law. Simon has been serving the central Virginia area since 1992.

Simon is a member of the National Academy of Elder Law Attorneys (NAELA), the Virginia Academy of Elder Law Attorneys (VAELA), and Lawyers with Purpose, a national organization of leading estate planning attorneys providing excellence in estate planning. He is also a member of various local chapters and other related legal planning organizations.

Simon has spoken on numerous occasions to organizations such as UVA Hospital (Neurology and Dementia units, Social Workers, Discharge Planners), The Alzheimer’s Association, JABA (Jefferson Area Board for Aging), accounting firms, financial planners, senior care planners, geriatric case managers, and various assisted living facilities and nursing homes. He offers monthly seminars on Elder Law, Estate Planning, Asset Protection, Medicaid Planning, and Veterans benefits in Charlottesville, Richmond, and Staunton.

In his spare time, Simon enjoys playing Pickleball, cooking, riding his motorcycle on the Blue Ridge parkway, and chasing after his yellow lab, Stryder. Above all, Simon relishes in the chance to spend time with his three adult children.

Lovely, beautiful people. Jeannie is always friendly and pleasant and informative. The office has perfect lighting, and we’re always offered tea or coffee. The whole experience, though it could be a time of anxiety, becomes a very loving, relaxing experience. Who knew that taking care of our family’s future and “late” life business could be such a nurturing, caring experience?

Edie G.
Gordonsville, VA

Everyone in the firm is friendly, knowledgeable and professional. All your needs will be taken care of in a timely manner, with everything explained thoroughly.

Tracy F.
Richmond, VA

Thank you for your wisdom, patience & support through this process. We always felt like we were in “good hands.”

Carol D.
Greene County, VA

Expedient, professional, and top-notch services. Extremely trustworthy and reliable. The best of the best.

Maria P.
Centreville, VA

Stapleton Elder Law is by far the best legal firm in our area. Their knowledge and skill is unmatched.

Leonard L.
Charlottesville, VA

I can say that I worked with Simon and his professional, awesome team and they have put my mind and heart to ease. Highly recommend.

Myra D.
Appomattox, VA

Met when needed legal assistance for multiple family issues. Defined and proceeded to structure medical, trusts and will to protect wife, son, and grandchildren. Also, have amended my trust and feel it’s important to join the C.F.C. Plan [the Client and Family Care Plan] for other expected services.
You owe it to your beneficiaries to have your life’s/death’s plans defined.

Robert M.
Nellysford, VA

Simon and his office are professional, knowledgeable, and gives their all to making sure you get what you need!

LeAnn M.
Charlottesville, VA

I found Mr. Stapleton very calm, thoughtful and a good listener. He helped me with my questions and concerns.

Jan B.
Charlottesville, VA

I have utmost faith in Simon’s knowledge of elder law and recommend him highly to anyone looking for expert guidance in this area.

Beth G.
Richmond, VA

What a great learning experience. Everyone there was always readily available and very knowledgeable.

Celia T.
Charlottesville, VA

Thank you for your concern and help in updating our legal documents. Being able to sign the papers in your office was great.

Jim and Mary A.
Waynesboro, VA

Working with Mr. Stapleton and his very excellent staff was a complete pleasure. The resulting documents reflect their knowledge & dedication. I highly recommend their services.

Tamsin S.
Charlottesville, VA

The entire staff is compassionate to all aspects of dealing with the often times difficult and sensitive matters of estate planning and planning for your elder years. Top notch. Couldn’t be more satisfied.

Brian S.
Charlottesville, VA

Great experience with Simon! He was efficient and professional. I can relax knowing that (my planning) is well taken care of.

Laura D.
Charlottesville, VA

We’ve known Simon for the last 2-3 years he has worked with us to resolve a number of complex family issues. Simon’s manner is gentle, kind and reassuring; he instills confidence. We have great peace of mind knowing that he’s there for us. We have recommended him and will continue to do so we consider him more than just our attorney.

Gene and Kim Y.
Scottsville, VA

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Stapleton Elder Law

866-284-4529    info@elderlaw-va.com

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Stapleton Elder Law is your Virginia resource for Asset Protection, Medicaid Pre-planning, Elder Law, Long-Term Care Planning, Paying for Nursing Home Cost Planning, Estate Planning, Business Owners and Business Succession Planning, Charitable Planning, Estate Tax Planning, Special Needs Planning, Veterans Benefits and Aid & Attendance. Stapleton Elder Law serves clients in Charlottesville, Virginia and the Surrounding Areas, including Winchester, Richmond, Staunton and more.
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